A dental polymerizable composition composed of a polymerizable monomer and a polymerization initiator has been widely clinically used at present. The dental polymerizable composition has been used, for example, in a dental restorative material which is so-called a composite resin usable in filling or repairing fracture of teeth or cavities of dental caries, a dental adhesive agent for adhering a crowning prosthetic such as a composite resin or inlay and crown to teeth, or cement, further artificial teeth or a denture base material, a coating agent, or the like.
However, when these resin-based restorative materials are present in the oral cavity for a long period of time, it has been pointed out that discoloration or coloration is generated on its surface, and plaque is likely to be deposited thereon. Also, when plaque is deposited on surfaces of natural teeth, without being limited to the restorative material, it is said to be causes of various oral cavity diseases such as dental caries or periodontal diseases.
In recent years, it has been tried to inhibit the deposition of the plaque by giving the surface of teeth or a restorative material anti-staining property, and a dental plaque-forming inhibitor comprising a polymer containing a monomer unit containing a phosphoric acid group and a monomer unit containing an oxyethylene group in the main chain has been proposed (see, for example, Patent Publication 1).
In addition, in order to inhibit the discoloration or coloration of the surface of the resin-based dental restorative material or the accumulation of the plaque, dental materials in which a fluorine-based material is applied, such as a coating agent comprising a silicone oligomer containing fluoroalkyl groups on both ends of the main chain as an active ingredient (see, for example, Patent Publication 2); a relining material for removable denture or a coating composition each containing a fluorine-containing (meth)acrylate as a part of the monomer (see, for example, Patent Publications 3 to 4); and a coating composition comprising a fluorine-containing polymer obtained by copolymerizing a monomer having a polar group such as acrylic acid with a monomer containing a fluorine atom (see, for example, Patent Publication 5) have been proposed.
Further, as an attempt of applying a fluorine compound to dental material applications for the purpose other than the anti-staining property, a glass ionomer cement curing liquid containing a poly(meth)acrylic acid having a fluoroalkyl group at both ends of the main chain has been proposed (see, for example, Patent Publication 6). In addition, when the scope is broadened to applications other than the dental materials, as techniques of imparting a base material with an anti-staining property, a technique of applying a polymer having a fluoroalkyl group on both ends of the main chain, the main chain being constituted by monomer units having a phosphoric acid group or an N,N-di-substituted aminocarbonyl group, as a surface-treating agent to fibers, metals, plastics, papers, and the like (see, for example, Patent Publications 7 to 9); a technique of applying a photopolymerizable coating agent composition comprising a polymer having a fluoroalkyl group on both ends of the main chain, and a photopolymerizable monomer or a prepolymer in the surface modification of plastics, wood materials, fibers, metals, and the like (see, for example, Patent Publication 10); and the like have been proposed.
Patent Publication 1: Japanese Patent Laid-Open No. 2003-48842
Patent Publication 2: Japanese Patent Laid-Open No. Hei 5-155730
Patent Publication 3: Japanese Patent Laid-Open No. 2000-312689
Patent Publication 4: Japanese Patent Laid-Open No. 2003-95838
Patent Publication 5: Japanese Unexamined Patent Publication No. Hei 10-510531
Patent Publication 6: Japanese Patent Laid-Open No. Hei 5-255032
Patent Publication 7: Japanese Patent Laid-Open No. Hei 10-7731
Patent Publication 8: Japanese Patent Laid-Open No. Hei 10-251348
Patent Publication 9: Japanese Patent Laid-Open No. 2003-253022
Patent Publication 10: Japanese Patent Laid-Open No. Hei 10-245419